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skz

For reference, Jeff is 34 here and Annie is 18. It's technically legal but really just not cool. Annie acts a little older than her age and Alison Brie was definitely older than 18 here but in real life this would be pretty uncomfortable.

Dr Ozzy

The Dalmatian story is a callback to S1E10 when it shows the dean watching a video on his laptop of a man in a Dalmatian suit and he says “this better not awaken anything in me” The “bring Conan back” quip from Star Burns was because this show was the time when Conan took over for Leno and then got his show taken away. The actor that plays Star Burns was a writer on for Conan.

Lars G

My rule of thumb with shows like this is to turn off the real world logic. I think applying real world sensibilities to sitcom plots/logic is going to twist you up in circles to no real benefit. In the real world the age gap is less then ideal, in the community tv show world it's a funny cliffhanger ending considering the plot of the rest of the episode. I don't think it's that deep.